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WO2008136018A3 - Nouveaux congénères de 4β-amino podophyllotoxine utilisés comme agents anti-cancereux potentiels et leur procédé de préparation - Google Patents

Nouveaux congénères de 4β-amino podophyllotoxine utilisés comme agents anti-cancereux potentiels et leur procédé de préparation Download PDF

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Publication number
WO2008136018A3
WO2008136018A3 PCT/IN2008/000256 IN2008000256W WO2008136018A3 WO 2008136018 A3 WO2008136018 A3 WO 2008136018A3 IN 2008000256 W IN2008000256 W IN 2008000256W WO 2008136018 A3 WO2008136018 A3 WO 2008136018A3
Authority
WO
WIPO (PCT)
Prior art keywords
podophyllotoxin
preparation
anticancer agents
anilino
benzothiazole
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/IN2008/000256
Other languages
English (en)
Other versions
WO2008136018A2 (fr
Inventor
Ahmed Kamal
Banala Ashwini Kumar
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Council of Scientific and Industrial Research CSIR
Original Assignee
Council of Scientific and Industrial Research CSIR
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Council of Scientific and Industrial Research CSIR filed Critical Council of Scientific and Industrial Research CSIR
Priority to GB0919517A priority Critical patent/GB2461667B/en
Priority to JP2010505015A priority patent/JP5355550B2/ja
Publication of WO2008136018A2 publication Critical patent/WO2008136018A2/fr
Publication of WO2008136018A3 publication Critical patent/WO2008136018A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

La présente invention concerne une nouvelle classe d'analogues de 4β-[4'-(1', 3'-benzothiazole-2'-yl) anilino] podophyllotoxine représentée par la formule structurale (4) dans laquelle R = H ou CH3 ; R2 = H, halogène, CH3 et R2 = H1, halogène, OCH3. La présente invention concerne également un procédé pour la préparation de nouveaux analogues de 4β- [4'-(1', 3'-benzothiazole-2'-yl) anilino] podophyllotoxine utilisés comme agents anti-cancéreux. L'invention concerne plus particulièrement un procédé pour la préparation de dérivés 4β- [4'-(1', 3'-benzothiazoIe-2'-yl) anilino] de podophyllotoxine. Le procédé pour la synthèse de nouveaux analogues de podophyllotoxine utilisés comme agents anti-cancéreux produit les nouveaux dérivés stéréo-sélectifs de la podophyllotoxine avec de bons rendements, l'étape clé pour la synthèse de ces analogues étant la substitution nucléophile directe d'intermédiaires C-4β-iodo. L'invention concerne également la 4β-iodopodophyllotoxine, qui a été amenée à réagir avec une 4-(1,3-benzothiazole-2-yl) aniline substituée ou non substituée de façon stéréo-sélective pour produire les dérivés 4β-[4'-(1', 3'-benzothiazole-2'-yl) anilino] de la podophyllotoxine.
PCT/IN2008/000256 2007-05-03 2008-04-23 Nouveaux congénères de 4β-amino podophyllotoxine utilisés comme agents anti-cancereux potentiels et leur procédé de préparation Ceased WO2008136018A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB0919517A GB2461667B (en) 2007-05-03 2008-04-23 4¼-amino podophyllotoxin congeners as potential anticancer agents and a process for the preparation thereof
JP2010505015A JP5355550B2 (ja) 2007-05-03 2008-04-23 抗癌剤として新規な４β−アミノポドフィロトキシン同属体とその製造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN953DE2007 2007-05-03
IN953/DEL/2007 2007-05-03

Publications (2)

Publication Number Publication Date
WO2008136018A2 WO2008136018A2 (fr) 2008-11-13
WO2008136018A3 true WO2008136018A3 (fr) 2009-03-12

Family

ID=39829038

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2008/000256 Ceased WO2008136018A2 (fr) 2007-05-03 2008-04-23 Nouveaux congénères de 4β-amino podophyllotoxine utilisés comme agents anti-cancereux potentiels et leur procédé de préparation

Country Status (4)

Country Link
US (1) US7960418B2 (fr)
JP (1) JP5355550B2 (fr)
GB (1) GB2461667B (fr)
WO (1) WO2008136018A2 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2638047B1 (fr) * 2010-11-11 2014-07-16 Council of Scientific and Industrial Research Dérivés de 4-beta-acrylamidopodophyllotoxin substitués en tant qu'antibiotiques antitumoraux et leur procédé de préparation
CN108285455B (zh) * 2017-08-16 2022-02-08 汤亚杰 4β-氨基取代鬼臼毒素类衍生物及其制备方法和应用
CN113402527A (zh) * 2021-06-22 2021-09-17 广东医科大学 一种鬼臼毒素结构修饰的衍生物及其制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5300500A (en) * 1989-02-23 1994-04-05 The University Of North Carolina At Chapel Hill 4 beta-amino podophyllotoxin analog compounds and methods
WO2004033423A2 (fr) * 2002-10-11 2004-04-22 Plantaceutica Inc. Composes anticancer

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5300500A (en) * 1989-02-23 1994-04-05 The University Of North Carolina At Chapel Hill 4 beta-amino podophyllotoxin analog compounds and methods
US5541223A (en) * 1989-02-23 1996-07-30 Yale University 4β-amino podophyllotoxin analog compounds and methods
WO2004033423A2 (fr) * 2002-10-11 2004-04-22 Plantaceutica Inc. Composes anticancer

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
XIAO-KANG ZHU ET AL.: "Antitumor Agents: 194. Synthesis and Biological Evaluation of 4-beta-Mono-, -Di-, and -Trisubstituted Aniline-4'-O-demethyl-podophyllotoxin and related compounds with Improved Pharmacological Profiles", JOURNAL OF MEDICINAL CHEMISTRY, vol. 42, 1999, pages 2441 - 2446, XP002507904 *

Also Published As

Publication number Publication date
US20080275248A1 (en) 2008-11-06
JP5355550B2 (ja) 2013-11-27
WO2008136018A2 (fr) 2008-11-13
GB2461667B (en) 2011-11-16
GB0919517D0 (en) 2009-12-23
US7960418B2 (en) 2011-06-14
JP2010526058A (ja) 2010-07-29
GB2461667A (en) 2010-01-13

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